He wants to be The Casanova, but he fails horribly. Maybe it's the polyester suit. Or the gold medallion around his neck. Or the phony "hey babe". Or the obvious hair plugs. Whatever it is, though, the girls see it from a mile away and give him a wide berth.

Sometimes the Casanova Wannabe talks a great game. He may have all his friends convinced that that he's the original ladies' man and that his bed is never cold. But the truth is, he still hasn't done it (or, if not, has only had bought-and-paid-for sex. Once. Which will be revealed in a pathetic and embarrassing tearful and/or drunken confession). The women can see the blinking neon "loser" sign bolted to his receding hairline a mile away. He clearly wants to prove his manhood, via Sex as Rite-of-Passage, but hasn't managed it yet. If he has a job, it's likely as a Lounge Lizard. In Real Life, the profane term "fuckboy" has become a current (likely soon to be outdated) slang term for irritating young real world Casanova Wannabe men, particularly those defined by a mix of boorish forwardness thinly disguised as flirtiness ("hehe and then what? ;)" and "wanna play the question game? ;)" being examples of their approach), mindgames that are designed to allow him to put in the bare minimum of effort required to continue extracting sex from his target, and a massive sense of entitlement.

Generally he's bound to succeed once or twice, by law of averages if nothing else. These relationships usually don't last long.

Ataru from Urusei Yatsura has a face only a mother could love (and even she sometimes regrets having him), and the worst luck possible. Nevertheless, he is always ready to ask a random girl off the street for her address and phone number. This despite having an alien beauty (who has electric powers and is deathly jealous, to boot - just do the math) for a fiancée. His main trait, though, is Cosmic Plaything considering how much he pays for this.

Bleach: Keigo loves women, especially if they have large breasts. He's never successful in his attempts to attract a single one.

Takamura Mamoru from Hajime no Ippo. The most infamous incident being him getting rejected in front of a Love Hotel. To make matters worse, a Paparazzi just happened to be there with a camera ready. Cue Amusing Injuries from Team Dad Kamogawa and horrified reactions from other boxers.

Brock (more Chivalrous Pervert) and Ash's Oshawott from Pokémon. (Fortunately for Brock, he usually has someone, usually Misty, Max or his Croagunk, to pull him away from a girl he hits on before he makes a complete fool of himself.)

Masomi Kida from Durarara!!. His attempts at wooing women fail to the point where even his partnerMikado lampshades his failures. However he stops when he gets back with his former girlfriend, Saki Miyajima.

Sunohara from CLANNAD has a bit of this. It is not helped by Tomoya and occasionally Kyou taking advantage of his gullibility and tricking him into thinking a girl is interested in him.

Is This a Zombie? has Orito, who thinks he's the epitome of the ladies man, and is completely oblivious to the fact that everybody thinks he's an annoying and creepy geek.

Jenos Hazard of Black Cat. Most of his appearances show him striking out while hitting on women, and his official character profile even remarks about how his success rate with picking up women is way lower than you'd assume of someone with his assets (which include good looks, a snazzy suit, and a prominent position in one of the most powerful organizations in the world).

Space Dandy from, well, Space Dandy spends much of his time thinking about beautiful women and trying to flirt with them. The thing is that said beautiful women are almost all far smarter, more skilled, and superior in combat than he is. That being said, he does manage to score a victory every now and then when Space Dandy's heart is in the right place. Meow would be one too if he hadn't already given up, content with taking voyeuristic photographs and browsing porn online.

Shimada from My Monster Secret not only fails to seduce any lady, he also has a rotten luck that borders on karmic with the ones he hits on. Ryou, his "girlfriend", is notably... a guy in a female Mobile-Suit Human, who is also a Casanova Wannabe. Later on, he tries to hit on his young and beautiful new teacher Ryokuenzaka Yumi; who turns out to be a giant male vampire in a female disguise. He's also a fan of Shiho, who switches genders when she sees the moon. Shima doesn't suspect any of that.

Comic Books

Viz (the comic book, not the Anime distributor) gives us Sid the Sexist, who, while not wearing a leisure suit, is very much a virgin despite his claims to the contrary and his attempts to change that situation. His friends could also possibly come under the same category - while they have occasionally been shown having success with women, usually they appear to look up to Sid for his 'studliness'. One strip even featured the brother of one of Sid's friends, who wore a leisure suit and claimed to be a massive hit with the ladies. Sid attempts to one-up him by getting several love bites - with the aid of a bicycle pump. He is, of course, caught and mocked by his friends. But then the last panel shows the friend's brother, alone in a tiny bedroom, doing the same trick, surrounded by porn magazines, used tissues, inflatable dolls and other sexual paraphernalia, making him possibly the only character to have ever been made to look even more pathetic and lonely than Sid in the strip.

Dean the pig from Liberty Meadows, where all the animals are anthropopathic, if not anthropomorphic.

Fillmore from Sherman's Lagoon goes to mating season every year at Ascension Island and consistently fails horribly.

Steve Dallas from Bloom County, who apparently thinks a box of obscenely-shaped chocolates will win a woman's heart (or at least get her to sleep with him). Though apparently he did eventually have sex with a woman, as his son Augie shows up in the sequel comic Opus.

Nate Wright, the titular character from Big Nate is a Kid-anova Wannabe. His combination of utter cluelessness and unwaning self-confidence when it comes to girls is a central theme in the comic.

The Brady Bunch: Greg's Big Man on Campus character from the original, Flanderized and comically made into a complete loser who is totally oblivious that he is a loser.

Charlie Chaplin's Tramp character in Mabel's Strange Predicament, the second film of Chaplin's career and the first in which he dressed up as the Tramp. In this one he's a drunken hotel guest who makes an ass of himself by hitting on all the women in the lobby and chasing poor Mabel Normand around.

Moe from Slap Shot. Every single thing he says has to do with sex and he has pictures from nudie mags taped to his locker. Yet he is never seen with a single woman at any point in the film. The weird goalie with a thick Quebec accent does better than Moe.

Colin Frissell (Kris Marshall) in Love Actually. His friend Tony calls him "a lonely, ugly asshole" but Colin is convinced that he's a "god of sex", and the problem is that British women are too stuck-up — if he went to America, he'd have a girlfriend "instantly". Subverted when it turns out he's right, to an absurd degree.

The Private Life of Don Juan features Rodrigo, a young man who is trying to copy the real Don Juan but can't even manage to get over a lady's balcony without tripping. The first time he's challenged to a duel by a jealous husband, he's killed.

Owen from Jurassic World. Barry hints that he's this in the video game, but one of his lines from the movie pretty much confirms this when he says this to Claire:

"You want a consult here or in my bungalow?

Middle of the Night: Lockman, a 60-year-old Dirty Old Man who brags about all the "tootsies" he's regularly bedding. Eventually he shamefully admits that he's been impotent for two years.

Literature

Demian: Emil Sinclair from Hermann Hesse's novel arguably fits this, as he talks the talk, but actually the only move he made was a crush on a store keeper. That happened during his school days. Later, he did have a brief romance...to his best friend Max Demian's mom. They actually even kissed, but that's it.

Carlos Ramirez from The Dresden Files fits this. He's a young, somewhat cocky, warden who is constantly bragging about his sexual exploits. None of which have ever happened, seeing that he's a virgin. Revealed hilariously by Lara Raith.

In Tim Dorsey's books about Serge Storms, a minor character is Johnny Vegas, who is handsome, wealthy, fun to be with...and cursed never to lose his virginity. He is always just about to, when circumstances (often caused by Serge) intervene.

Larry Dallas of Three's Company is named Larry and may even be the inspiration for the computer game, but had too much (read: more than one) actual success with the ladies to really exemplify the trope. Mr. Furley probably qualifies though.

Herb Tarlek of WKRP in Cincinnati is on the fringe of Larry-dom since he's married and has kids. However, he does have the bad suit, attitude, and lack of success necessary to play the part.

The Young Ones: Mike, the self-proclaimed stud, was revealed in one episode to be a virgin. But given the show's Negative Continuity it's hard to say whether that really counts.

Murdock tries this in an episode of The A-Team when Face briefly leaves the team. Keyword, tries.

The Todd from Scrubs may be the ultimate Casanova Wannabe, especially after he comes to terms with his bisexuality. And possible anything-sexuality:

The Todd: Whoa, these are hot. [referring to two pieces of broccoli] Turk: Please tell me you mean temperature-wise, because there's no way you could find broccoli sexy. The Todd: Oh yeah, temperature-wise... and miniature-green-boobs-wise! [rubs his face between the two heads of broccoli]

Todd regularly boasts a great track record and hits on or makes innuendo at anything that moves. When pressed by The Janitor with "God is watching. How many times have you had sex in the last year?", he confesses none. Many women at Sacred Heart claim to have never slept with the Todd despite reputation, but they have proven to be extremely defensive about the idea to the point of suspicion.

Todd: Hey, Lisa. I heard you lied and said we didn't do it. Admit it. We doinked. Lisa: I was sad because my dad died. Todd: I wasn't.

This is debatable however. As Ted McGinley points out in the Reunion Special: "Bud was pretty successful because he had the greatest looking girls, week to week." This just isn't acknowledged in the series because of its Negative Continuity. It's just his success rate that's low, which isn't surprising considering he tries to get some in every episode.

In an episode where Al and Peggy split up, Al and his buddies tried to hit the club scene. Al got a makeover and became the definition of Casanova Wannabe. He also got a prosthetic ass.

However, when he gets the opportunity he always turns it down including a "shoe groupie".

He has had notable success, perhaps too much to be considered the Cananova Wannabe; besides the Daxii, there's a long but not deep relationship with Leeta, and briefer affairs with the mute genius girl and that weightless chick.

Dr. Zimmerman, inventor of the Holodoc, certainly qualifies in his appearance on Deep Space Nine.

Jay from the British cult sitcom The Inbetweeners, who makes near-constant boasts about his sexual expertise despite his obvious virginity. Jay a bit of a vague case, though, as he rarely ever talks to girls. He apparently prefers to brag to his male friends about his exploits instead. But when he does try to chat up girls, they don't usually seem interested (except for Chloe).

Will alternates between this and Kavorka Man. He does score with Charlotte - the school's most popular girl - and his hot, former babysitter, but he screws up before any of them manages to take his virginity. And when he tries to pull a nice and down-to-earth girl, Lauren, he fails spectacularly, especially by trying to imitate Yoda. He doesn't have much luck with Rachel either as he, according to the guy Rachel flirts with instead, "talks like they do in old movies".

Subverted on Burn Notice - even though Sam acts, dresses and looks like an archetypal Cananova Wannabe, he's actually successful with the ladies, although he uses his charms to woo rich divorced housewives who buy him nice stuff.

The two guys that Chris Kattan and Will Ferrell played in the Butabi Brothers sketches on Saturday Night Live. In the awful movie, A Night at the Roxbury, they were named Doug and Steve Butabi. Other examples of a Cananova Wannabe on Saturday Night Live include:

Christopher Walken's "The Continental"

Chris Parnell's "Merv the Perv" (who also had a brother played by Johnny Knoxville named "Irv the Perv")

The Woman Watchers (played by frequent host Tom Hanks and cast member Jon Lovitz, from the mid-1980s SNL)

The original "Two Wild And Crazy Guys!" (also played by a cast member and a frequent SNL host, only this time, it's Dan Aykroyd [the cast member] and Steve Martin [the frequent host])

Subverted with Larry (hmm, Shout-Out?) from Buffy the Vampire Slayer, who displays this behavior for a while, only to have it revealed that it's all an act, and he's actually gay. After he comes out to Xander (in private) he drops the act, though he is never seen to come out publicly on-screen.

Buffy also toyed with the idea in "Teacher's Pet"; one of the victims was very embarrassed when told that the mantis only attacked virgins.

Yo soy Betty, la fea provides us with two: NicolÃ¡s Mora, nerd extraordinaire and self-assumed ugly, who nonetheless still tries to hit on pretty girls and constantly woo Patricia Fernandez; and Freddy, the motorized messenger of Ecomoda, who, while better looking (and best dressed) than NicolÃ¡s, still exudes a big "loser" aura. Freddy manages to have an on-off relationship with Aura Maria, the hot receptionist of the company, but he inadvertently and constantly ruins any progress he does with her thanks to his misguided flirting towards the models who flood the place.

On How I Met Your Mother Barney flips back and forth between this and The Casanova, with a bit of Handsome Lech thrown in. On the one hand, he is quite handsome, dresses in legitimately stylish suits, and the notches on his bedpost are well into the triple digits. However, a lot of his pickup attempts can be pretty darn cheesy, it's clear that he's not always truthful about his sexual conquests, and, since the entire series is a story told by a potentially Unreliable Narrator, separating the lies from the truth isn't so easy.

At one point, Marshall actually calculates that, given the number of women Barney's slept with, compared to the sheer number of women he hits on, his success rate is actually only a little over 1%, despite having slept with more people than the rest of the main characters combined.

Tom Haverford from Parks and Recreation is a special case. In the first season he tells the documentary crew that he and his wife have an open marriage and that they're both disappointed he's not a more successful adulterer. His utter failures to pick up women are often shown. In the second season, Ron learns that Tom's wife is Canadian, and only married him to stay in the country.

His buddy Jean-Ralphio qualifies as well.

Friends: Played with with Chandler. He teases Ross who is desperate to get married again, envies Joey for being The Casanova, tries for a few one night stands himself and has Commitment Issues. However even early episodes have him ending no-strings-attached sex because he wants a relationship, and trying to keep a steady girlfriend. Most of his Commitment Issues stem from fear of being hurt, rather than wanting to play the board, and he's ten times happier after falling in love with Monica and being the first of the guys to get married.

Jackson Stewart of Hannah Montana has tried every cheesy pickup line and hare-brained scheme in the book to get girls. Mild subversion in that he has a fair amount of success, but rarely makes it past the first date.

Mr. Lucas from Are You Being Served? fits this trope. Despite being good looking and always claiming to be lucky with the ladies, he never seems to have much luck with them on the actual show.

Nathan from Misfits tries to chat up virtually every girl he meets, with very limited success. And when it does work, something usually goes spectacularly, mind-bogglingly wrong - e.g. one of his love interests is revealed to be an 82-year-old in disguise, mid-coitus. But most girls just seem disgusted with him on sight and immediately ignore or reject him. That said, he's undoubtedly only a Cananova Wannabe in-universe - among the fans he's easily the most popular and lusted-after character on the show, despite his obnoxious personality.

Pierce from Community obnoxious attempts to hit on Shirley and to a lesser extent other female students. However, the audience is shown he is a skilled seducer when he needs to be.

Whenever Winston Rothchild plays the Possum Lodge Word Game on The Red Green Show, Red gets the correct answer out of him by mentioning one of his past dates. Winston's words, for the record, are usually along the lines of "disaster" (in fact, that was one of his words).

Ethan, Benny, and Rory from My Babysitter's a Vampireand HOW. Every episode has multiple examples of their romantic failure. (Though in his defense Ethan is no where near as bad as Benny, and Benny in turn isn't as bad as Rory.)

Bobby Lee’s character Tank, from Mad TV, is a clear example. Despite his many elaborate attempts to score with women, he remains a virgin.

Paramedic John Gage on Emergency! gets teased for being this by Fireman Chet Kelly who doesn't seem to do any better with women.

Scandal: Stephen, though he seems to have mostly settled down. He still has an interesting past.

A Mr. Show sketch, has Lyle, one of the scientists living in the biosphere. On New Year's Eve, he tries asking out all the women, who all reject him. Seems like he's gonna be alone on New Year's . . . until he gets a visit from his step-Fairy Godmother.

Its Always Sunny in Philadelphia: Zig-Zagged with Dennis Reynolds. Sometimes he's good with the ladies, other times he's this trope. Both reactions are justified because he has been able to function socially more than the rest of the gang which isn't saying much. However he also has been shown to be the most depraved member of the gang and has little understanding of human relationships. He also gets mistaken for a gay man when he hits on a married woman by gossiping about her husband and wearing make-up and a girdle. On a dating website, he gets 0 Stars.

Jerome, one of the many characters Martin Lawrence played on his television series, is a man in his late 40s who is going through a major mid-life crisis. He believes himself to be the ultimate player and that all the women want him, especially Martin's wife, Gina. It's all in his head, however, and a lot of hilarity ensues. He even has his own theme song.

The title character of "My Name Is Eugene" by Crazy Joe & the Variable Speed Band.

It's unclear how successful Jon Lajoie's character of MC Vagina is at winning over women, but his awful singing, blatant sexism, and laughably bad pickup lines (he considers a song for the ladies to be one entitled "Show Me Your Genitals") would probably doom him in any sane world. Notably, despite his claims of having wooed women around the world with his twenty-five-inch penis, the only time he's ever seen onscreen with women is in "Very Super Famous," and they were decidedly not head-over-heels.

Pro Wrestling

WWE tried to give Dean Malenko a ladies' man gimmick after the Radicalz broke up, but he was too short and too old to be believable in the role.

Austin Aries told a fan heckling him at ROH The Final Showdown that if he wanted her mouth open he'd have dropped his pants. That was before he took on the (admittedly Lighter and Softer) "A Double, The Greatest Man Who Ever Lived" gimmick in Chikara.

Zack Ryder, a gullible, self-absorbed, outspoken loser who will often pick up and lose a WWE 'Diva' escort over the course of a show.

"Prince" "Wonderful" Xander has probably always had traces of this trope about him but it really went to his head in the World Wrestling League.

After his CMLL debut, Matt Taven proclaimed he had come to the land of trios in preparation for winning the ROH Six Man Tag Tournament at Final Battle, adding

"There can only be one first, ask your girlfriend."

Theater

The Cashier in The Most Happy Fella unsubtly announces his eligibility to the waitresses. The heroine makes her first entrance in the show by rejecting his advances violently.

Video Games

Of course, the eponymous Leisure Suit Larry, the former Trope Namer. He is basically a 40-year-old virgin in the first game, loses his virginity, but doesn't get a steady girlfriend. The general formula is Leisuresuit Larry manages to get the girl after going through many absurd hurdles at a game's end, only for the next game to begin with Larry getting dumped. For example even after winning a contest to spend a week with the attractive woman captain at the end of one game, Larry has to bribe her with a large stock in oil hauling.

Super Robot Wars Advance: Axel Almer, when picked as the protagonist, becomes some sort of this, flirting with every girl he sees and failing horribly in each attempt. For example, when he is asked for his name by Sayaka Yumi, his answer was: "Maybe I'll remember my name if a beautiful girl like you kisses me". This added more reasons why he's called Ahoseru.

Not to mention a 4koma re-enacting this scene (when Axel and Sayaka are in their respective mechs) has a Rocket Punch belting Axel's mech immediately from nowhere. Hilarity Ensues, indeed.

Greg, one of the colonists in Space Colony. With the voice of a late night radio personality and pick-up lines out of a Saturday Night Live sketch, Rick is an utter failure when it comes to women, even when compared to Mad Scientist Nicolai and Disco Dan Charles. He's a flagrant misogynist and is regarded with unmasked contempt by main character Venus; Even his official company profile paints him in an unflattering light. He's also one of the least useful colonists, having high standards for happiness and few strong skills.

Greg, as it happens, appears to be based on a similar character from MADTV.

An elf called Salvanas, who can be found in a bar, is a minor character whose only function is to hit on every female party member that talks to him (except Imoen, who was added at the last moment). Salvanas flirts so blatantly shamelessly that he's inevitably angrily rejected. The only one interested is a temporary female Edwina—but after Salvanas's verbal slip she gets angry and kills the poor elf. If a female player character chooses not to reject him, Salvanas gets scared and runs away.

A wizard Edwin hits on some female party members (including Mazzy the halfling!) and likes to talk about many concubines he left gasping after his erotic onslaught. In truth... well, it appears that in Athkatla he's had a fling with a barmaid, who finds him very cute.

Jak and Daxter: Daxter is like this. He flirts with every attractive female in the series, despite the fact that he's been turned into a three-foot-tall rodent. He seems to have grown out of it by Jak X, though it might just be because he finally has a girlfriend.

Carlos Olivera from Resident Evil 3: Nemesis, famous for the memorably cheesy line "All the foxy ladies love my accent. It drives 'em craaaazy!" Jill, however, is already quite smitten with her task of avoiding a gruesome, horrible death, so depending on where she meets Carlos, she'll either shoot down his flirting or simply ignore it.

Junpei from Persona 3, who tries to make up for with sheer bravado what he utterly lacks in everything else when it comes to women. The ladies still aren't impressed.

Rock from Harvest Moon: Another Wonderful Life is this, to the point of even wearing a leisure suit and calling the main character "babe". He fails miserably at romance (though he fancies himself quite the catch) which is lampshaded by his mother, who questions your mental health should you pursue him.

Dragon Age: Origins: Oghren imagines himself as being quite the ladies' man, though most of the females he hits on find him utterly repulsive. He was married, though his first wife left him and then fell in love with another woman. He then started up a relationship with Felsi, who was quite a looker ... and also dumped him. In truth, there is some hint that Oghren's lecherous behaviour is a cover for his crippling insecurities.

Ewan Devlin from Mercenaries 2: He believes that he's a smooth-talking Irish stallion, but as evidenced throughout the game, he often drives the girls away by talking their ears off, hitting them with a bust of the Big Bad, or by detonating something in the stockpile.

Agarest Senki gives us Winfield and Thoma. Winfield is a textbook case of this trope. Thoma however actually has a crapton of game and earns the ladies company. Too bad Winfield taught him how to treat a woman which leads to Thoma starting off strong then halfway becoming like Winfield.

To put this into perspective Thoma said the wrong thing TWICE to a Tsundere. In the same sentence. While she told him to buzz off. He still convinced her to hang out with him yet Winfield's brainwashing led to another sexual comment. He manages to leave unscathed due to turning her anger to exasperation. Thoma got game, his teacher just programmed him not to use it consistently.

Interestingly, the one time he does get a chance to have sex (with a woman who hasn't seen a man besides her brother for twenty years), he backs out because he thinks the most common target of his flirtations, Miss Pauling, will like him better if he waits.

Another oddity (though he may be lying), he's actually good with girls (at least in regards to casual sex), as shown by a flashback in Expiration Date. Problem is, in his words, it's the ladies that he wants, and can't have.

Ringabel in Bravely Default hits on every woman he encounters and manages to annoy everyone around him in the process, including most of the women he tries to flirt with. The other members of the party put up with him because he's the only one who can pilot their airship. Played with in that only major female characters, the ones with names, react to him this way, and he has absolutely ridiculous amounts of success with minor female characters. He was extremely successful manipulating the hair dye saleswoman for information before Edea ruined it, and he's implied to have dated at least a dozen women offscreen, sometimes multiple at the same time.

Inigo and Virion from Fire Emblem Awakening make an effort to go after every woman they can, despite the fact they're in a war. Inigo has his reasons, though, considering that the reason he's such a ladies man is because his dead future mother told him to talk to women to not be so shy and anxious all the time.

"Big" Tom from Fear Effect 2: Retro Helix. His 2 cut scenes consist of nothing but a bunch of lame come ons directed at Hana, much to her disgust. One gets the feeling if they weren't in a crowed room, she'd have shot him.

Valdis Story: Abyssal City has Vladyn, who has made "weak advances" on at least two of his crewmates, and tries it on again with the first female NPC he meets.

Web Animation

Despite his claims of prowess with the "lady-types", Strong Bad from Homestar Runner is definitely a Cananova Wannabe. In one e-mail, he slips, and admits "I don't really know anything about the ladies either... I mean I do! I mean... WHGT! JGTH! YES I'M AWESOME!"

Tucker from Red vs. Blue is a shining example of this trope. Unfortunately, the only women he sees on a regular basis are ruthless super soldiers who would kill you as soon as look at you. In fact, the only action he gets during the story is with Grif's sister (or so he claims) and a Face Full of Alien Wing-Wong. (The latter, note, was only implied in hindsight by later events; at the time, everyone just thought Tucker was being beaten up.)

Neomutant from "TOME" is said on the TOME Character page to fancy himself as being charismatic. Though if his success with Flamegirl is anything to go off of, right down to scaring her straight into the arms of her love interest Alpha, he is far, far, far from successful as a Casinova.

RWBY: Neptune has worked very hard to build a "cool dude" persona that includes hitting on every pretty girl he meets. Yang doesn't seem to notice his appreciation of her, Melanie and Miltia dismiss his approach entirely, but Weiss is impressed by him, much to Jaune's disbelief, as Neptune's moves on Weiss were actually the same as Jaune's. Neptune eventually admits to Jaune that he's hiding a completely dorky interior which puts him off pursuing Weiss more seriously. Jaune sets him straight, giving up his own attempt to woo Weiss in the process.

Robin DeSanto of the Walkyverse may qualify as a female version (just for being so much of a No Social SkillsGenki Girl), especially with the recent Reveal that she's a virgin. She is pretty attractive, though.

Smug Snake Faz owns this trope in the Walkyverse; he's both certain he's a lot more attractive and desirable than he in fact is (the permanent expression of self-satisfied smugness doesn't help) and is absolutely convinced that one day he and Amber will enjoin together in passion. He isn't going to let the fact that Amber openly and loudly detests him and everything about him dissuade him.

What about the fact that they are probably related?

In Misfile this trope is filled by Colin the Counter Guy in the local autoparts store.

Eastwood in Exterminatus Now, who regularly suffers great physical harm from hilariously crude attempts at hitting on anything with a skirt. Probably the reason why he has the biggest Porn Stash in the world.

On such a scale that he's begun to acclimatize to pepper spray.

Femmegasm: June, in a rare female variety. Most people don't find monkeys with a large amount of distressingly long, thick body hair attractive, which means her attempts to get laid pretty much always end in rejection.

Eridan Ampora from Homestuck is practically the classic example. Being from a naturally bisexual species, his options are a bit more widely-ranging than most. Doesn't do him any good, though - not only is he rejected every time he tries, but by the time he dies, he doesn't have any romantic relationships at all. Even his moirail has dumped him, fed up with his narcissism and his constant threats of genocide.

Cronus's example is made especially sad when he actually hits on Eridan. Even Eridan is able to immediately pin him as trash, but ultimately accepts his advances out of very blatantly stated desperation.

Both are so pathetic they can't even form a blackrom with anyone. Everyone hates them, but in the "stay away you creepy loser" way and not the "I love to hate you" way.

PvP's Robbie had all the standard cheesy pick-up lines and zero success with women in his earlier strips. His buddy Jase was much more realistic about the potential desirability of a couple of beer-guzzling couch potatoes.

Aaron West in Forever16, gets kind of sad knowing that a theoretical Time Skip would have him still be this.

All the women in the Espionage theme of Irregular Webcomic! believe that James Stud is an annoying buffoon, however much he attempts James Bond's pick-up lines.

Collin of White Dark Life is an exaggeration of this. He believes he is attractive but his giant ego and weak physical stature quickly turn off any woman he has interest in, including Horny Devils. And then it turns out his soul holds traces of pure chastity to boot, which guarantees this status.

Later, Kris takes this role from Collin once the later cleans up his act. Only natural considering he's an incubus with pride as his main trait.

The fool concerns himself with the 99 who say "no", while the wise man comforts himself with the one who says "yes".

Web Original

Valentin from Noob regularly tries to pick up women with extremely cliched pick-up lines the second he meets them and continues trying when they show to not be interested. Laser-Guided Karma has hit him both in the webseries and novel version via the story being set in a MMORPG in which Cross Playing isn't unheared of.

Suave, one of Bennett the Sage's alternate characters on Anime Abandon, complete with smoking jacket, glass of scotch, and doing his best to channel Hugh Hefner although he usually just comes off as a sleazy git. He pops in every now and then to make jokes about the naughtier aspects of some of the anime featured on the show, and hosted it for the reviews of Golden Boy and Eiken.

Contra Points examines the "pick up artist" type in one of her videos. It's pretty depressing, since the modern version doesn't seem to be about enjoying sex or liking women, but trying to prove something by entering a "conquest" into a spreadsheet.

It is implied that Homer Simpson from The Simpsons was like this before he met Marge, as evidenced by the time Lisa wanted advice on how to tell a guy you aren't interested:

Homer: Let me handle this Marge, I've heard them all. "I like you as a friend", "I think we should see other people", "I no speak English", "I'm married to the sea", "I don't want to kill you, but I will..."

Quagmire manages a good deal of success, but he's also failed enough times to not only develop an immunity to mace, but also to be able to tell different types of mace apart.

Brian is also this, usually with more failures. Not only does he act like a tool just to impress women, he's also known to date really stupid women so he can feel smarter than them and have an easier time getting in their pants, along with hitting on Lois several times. He has been called out on this as well.

Like Quagmire above, Boomhauer from King of the Hill is a partial example: he manages to have sex with lots of women, but one episode reveals that his method is to just hit on every woman he can find, usually with lame pickup lines, until he finds one that will give him the time of day. Bobby points this out to him, but Boomhauer's basic philosophy apparently is that one shouldn't let rejection get you down, though one episode had Boomhauer fall in love with a woman who only saw Boomhauer as a one-night stand and rejected his offer to marry her; man, he was dang ol' devastated, tell you what.

Martin Tubbs in W.I.T.C.H. - in the episode "H is for Hunted", he goes as far as to wear a leisure suit in an attempt to impress Irma.

Whenever Dr. Thaddeus S. "Rusty" Venture of The Venture Bros. breaks out the hairpiece and polyester vest, you know you're in for a night of "Rusty's back!", despite the fact that he was never there. He's not a virgin - he wouldn't have sons if he was - but he sure acts like it. Of his two known sexual encounters, neither was exactly healthy.

Shake is quite similar, to the extent that he vastly overestimates his own sex appeal. Oddly enough, Frylock has accidentally given himself away, a few times, as depressingly incompetent with women even when Shake and Meatwad aren't around to kill the moment.

Futurama: Zapp Brannigan. He sure acts like a stud. But on first meeting Leela in "Love's Labours Lost in Space" she ends up having pity sex with him; This is later revealed to be his first, and for some time after, only sexual encounter. (The second was something he probably would have liked to forget...)

Odd from Code Lyoko. He claims to be a ladies man, but while he has dated most girls in his age group at Kadic, they all say otherwise. (In fact, the only girls that he can truly call friends are Yumi and Aelita, and neither is a girlfriend in any true sense.) Part of his problem might be the whole "dated two girls at once" thing that Yumi unfortunately took the fall for (due to being in his body at the time).

In Gravity Falls episode "Roadside Attraction", Stan gives Dipper advice on how to talk to girls, claiming to be an expert on the subject. At the end of the episode, Stan's forced to admit that he's anything but. The end-credits cryptogram states that Stan's best relationship was with an animatronic.

Stan: Alright, kid. I gotta admit something. I'm no expert on women. Truth is, I've been divorced once, and slapped more times than I can remember. Confidence can buy you a lot, but at the end of the day, pickup artists tend to get our heads bitten off. When it comes to women, I'm a failure.

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